(E)-3-(N-methyl-N-p-tolylhydrazono)-2-pentanone | 653571-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-(N-methyl-N-p-tolylhydrazono)-2-pentanone
• 英文别名: (3E)-3-[methyl-(4-methylphenyl)hydrazinylidene]pentan-2-one
• CAS: 653571-36-9
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: YXWVWATUPWJONY-BUHFOSPRSA-N

物化性质

• 沸点：
  329.5±35.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.67
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  苯氧乙酰氯 、 (E)-3-(N-methyl-N-p-tolylhydrazono)-2-pentanone 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以63%的产率得到(3RS,4RS)-4-acetyl-4-ethyl-1-(methyl-p-tolyl-amino)-3-phenoxy-2-azetidinone
  参考文献：
  名称：

  α-Oxohydrazones as imine component in the synthesis of 4-functionalized azetidinones by the Staudinger reaction

  摘要：

  1-(Methyl-p-tolyl-amino)-3-phenoxy-2-azetidinones 4-COX and 4-R substituted (COX: X=Me, Et, Ph, NMe2, NEt2, OBu'; R=Me, Et, Ph) were smoothly prepared from the corresponding alpha-(methyl-p-tolyl)hydrazonylated ketones, amides and esters via [2+2] cycloaddition with phenoxyketene. The reaction was generally high-yielding and diastereoselective, leading to beta-lactams with a cis relationship between the PhO and the COX moieties, except for R=Ph, where an opposite stereoselectivity was instead observed. The azetidinones represent interesting intermediates which couple protection at N(1) and functionalization at position 4 of the ring. Deprotection of N(1) can be easily attained by oxidative N-N cleavage with magnesium monoperoxyphthalate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.072
• 作为产物：
  描述：

  (Z)-(4-methylphenyl)azo tert-butyl sulfide 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 生成 (E)-3-(N-methyl-N-p-tolylhydrazono)-2-pentanone
  参考文献：
  名称：

  An easy access to 2-oxohydrazones via electrophilic α-p-tolylhydrazonylation of ketone enolates with tert-butyl p-tolylazo sulfide

  摘要：

  The title reaction conveniently furnishes, as the sole or main products, alpha-(p-tolylhydrazono)ketones or their N-methylderivatives (H+ or Mel quenching of the final mixture, respectively). Although the method fails with ketones having a secondary alkyl group bonded to the carbonyl, yields are otherwise more than satisfactory and particular interest is attached to the hydrazonylation of the methyl group in methyl ketones.

  DOI：

  10.1016/s0040-4020(01)89426-6

文献信息

• DellErba Carlo, Novi Marino, Petrillo Giovanni, Tavani Cinzia, Tetrahedron, 50 (1994) N 38, S 11239-11248
  作者：DellErba Carlo, Novi Marino, Petrillo Giovanni, Tavani Cinzia

  DOI：——

  日期：——